WHY YOU’RE GOING: Halfway between L.A. and San Francisco, San Luis Obispo is still a relatively hidden gem along California’s Central Coast. The quaint, blissfully uncrowded college town, home to Cal Poly SLO, is the perfect place to lay low for a few days, soaking up its leisurely (yet still lively) vibe. Spend the weekend walking the tree-lined downtown, where boutiques abound, wine flows, and farm-to-fork cuisine is fueled by SLO’s close proximity to California’s agricultural epicenter. It’s been called “America’s happiest city” for a reason.

WHERE TO STAY: You only live once, so you should definitely experience the Madonna Inn. Just a few minutes from downtown SLO, this wonderfully weird hotel has been a tourist destination for decades, beckoning travelers with more than 100-themed rooms and suites that follow a more-is-more ethos. Go back in time and stay in the Fabulous Fifties room (think Ozzie and Harriet beds) or book the Rock Bottom room to find out what it feels like to sleep in a cave. Check out the gift shop and the assorted pink pastries at the bakery. (100 Madonna Rd; 805 543-3000)

WHERE TO EAT: Thanks to abundant local produce, SLO’s food scene is one California’s most vibrant. Celebrate the fact that you’re in wine country with dinner at Koberl at Blue. Every menu item—from potato and onion pierogi with smoked salmon and sour cream to grilled pork chops with pancetta—has a recommended wine pairing, and the wine list includes some of the region’s best. Save room for fresh-fruit desserts like the strawberry sundae and a warm apple tarte tartin. (998 Monterey St; 805-783-1135)

WHERE TO DRINK: If you still have it in you after a day of wine tasting, Sidecar is a great place to relax with a drink. The saloon-style bar with its mismatched chairs and good-times attitude attracts an animated crowd. Try the Persimmon-On-On, a cocktail made with persimmon-cinnamon puree and grapefruit juice, or the self-titled Sidecar with cognac and orange curaçao. Stay for dinner or even just a few small plates—the fried brussels sprouts punched up with garlic aioli and blue cheese are insanely good. (1127 Broad St; 805-540-5340)

WHAT TO DO: While a day shopping downtown SLO’s indie boutiques and vintage stores is a must, carve out some time to visit Mission San Luis Obispo de Tolosa. This 1771 structure, with its arched doorways and meticulously kept grounds, is considered one of the most beautiful missions in California. (751 Palm St, 805-781-8220)